Radical-mediated click-clip reactions

IF 44.7 1区综合性期刊 Q1 MULTIDISCIPLINARY SCIENCES

Science Pub Date : 2024-09-19 DOI:10.1126/science.adn2259

Jiantao Zhao, Huacheng Yu, Xingchen Jin, Bo Qin, Shan Mei, Jiang-Fei Xu, Xi Zhang

引用次数: 0

Abstract

Click reactions, which are characterized by rapid, high-yielding, and highly selective coupling of two reaction partners, are powerful tools in synthesis but are rarely reversible. Innovative strategies that reverse such couplings in a precise and on-demand manner, enabling a click-clip sequence, would greatly expand the technique’s versatility. Herein, a click and clip reaction pair is demonstrated by manipulation of a sulfilimine linkage. Phenothiazines and amines are rapidly and quantitatively coupled through oxidative sulfilimine bond formation with N-bromosuccinimide, and the resulting sulfilimine bromides then undergo quantitative reversion to the phenothiazines and amines through photoreduction at 380 nanometers. This protocol enables fabrication of depolymerizable macromolecules and reversible modification of aminosaccharides, demonstrating high selectivity and efficiency for manipulating sulfilimine linkages in complex systems.

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自由基介导的单击夹反应

点击反应的特点是快速、高产和高选择性地耦合两个反应伙伴，是合成中的强大工具，但很少是可逆的。能够以精确和按需的方式逆转这种偶联反应、实现点击-剪辑序列的创新策略将极大地扩展该技术的多功能性。在此，我们通过操纵一种亚氨基磺酰亚胺连接，展示了一种点击和剪辑反应对。吩噻嗪和胺通过与 N-溴代丁二酰亚胺形成氧化亚磺酰亚胺键而快速定量偶联，然后通过在 380 纳米波长下进行光还原，将生成的亚磺酰亚胺溴化物定量还原为吩噻嗪和胺。这种方法可以制造可解聚的大分子，并对氨基糖进行可逆修饰，在复杂体系中处理亚磺酰亚胺连接具有高选择性和高效性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Science 综合性期刊-综合性期刊

CiteScore

61.10

自引率

0.90%

发文量

审稿时长

2.1 months

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